Ferrocene-derived bioorganometallic chemistry: Preparation of a [3]ferrocenophane γ-amino acid for use in peptide synthesis

Organometallics

Volumn 27, Issue 17, 2008, Pages 4269-4272

  Tebben, Ludger ^a   Bussmann, Kathrin ^a   Hegemann, Michael ^a   Kehr, Gerald ^a   Fröhlich, Roland ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; IRON COMPOUNDS; ORGANIC ACIDS;

BIO-ORGANOMETALLIC CHEMISTRY; FERROCENE; FERROCENOPHANE; LITHIATION; PEPTIDE SYNTHESIS;

QUENCHING;

EID: 52649098433     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8004542     Document Type: Article

References (47)

1. Ferrocene derived amino acids: Schlögl, K. Monatsh. Chem. 1957, 88, 601-621.
2. Hauser, C. R.; Lindsay, J. K. J. Org. Chem. 1957, 22, 1246-1247.
3. Herrick, R. S.; Jarret, R. M.; Curran, T. P.; Dragoli, D. R.; Flaherty, M. B.; Lindyberg, S. E.; Slate, R. A.; Thornton, L. C. Tetrahedron Lett. 1996, 37, 5289-5292.
4. Butler, I. R.; Quayle, S. C. J. Organomet. Chem. 1998, 552, 63-68.
5. Okamura, T.; Sakauye, K.; Ueyama, N.; Nakamura, A. Inorg. Chem. 1998, 37, 6731-6736.
6. Dialer, H.; Polborn, K.; Ponikwar, W.; Sünkel, K.; Beck, W. Chem. Eur. J. 2002, 8, 691-699.
7. Heinze, K.; Schlenker, M. Eur. J. Inorg. Chem. 2004, 2974-2988.
8. Moriuchi, T.; Hirao, T. Chem. Soc. Rev. 2004, 33, 294-301.
9. van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931-5985.
10. Kirin, S. I.; Kraatz, H.-B.; Metzler-Nolte, N. Chem. Soc. Rev. 2006, 35, 348-354.
11. Barisic, L.; Cakic, M.; Mahmoud, K. A.; Liu, Y.; Kraatz, H.-B.; Pritzkow, H.; Kirin, S. I.; Metzler-Nolte, N.; Rapic, V. Chem. Eur. J. 2006, 12, 4965-4980.
12. Chowdhury, S.; Schatte, G.; Kraatz, H.-B. Angew. Chem. 2006, 118, 7036-7038;
13. Angew. Chem., Int. Ed. 2006, 45, 6882-6884.
14. Lapic, J.; Siebler, D.; Heinze, K.; Rapic, V. Eur. J. Inorg. Chem. 2007, 2014-2024.
15. Jaouen, G.; Top, S.; Vessières, A.; Alberto, A. J. Organomet. Chem. 2000, 600, 23-26.
16. An overview of ferrocene-peptide conjugates on medicinal organometallic chemistry: Metzler-Nolte, N. Chimia 2007, 61 (11), 736-741.
17. For further examples of ferrocene derivatives in bioorganometallic chemistry, see e.g.: Metzler-Nolte, N., Salmain, M. The Bioorganometallic Chemistry of Ferrocene. In Ferrocene. Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; Wiley-VCH: Weinheim, Germany, 2008; pp 499-639.
18. Jaouen, G., Ed. Bioorganometallics: Biomolecules, Labeling, Medicine; Wiley-VCH: Weinheim, Germany, 2006.
19. Metzler-Nolte, N. Nachr. Chem. 2006, 54, 966-970.
20. Erker, G. J. Organomet. Chem. 2007, 692, 1187-1197.
21. Synthesis of three-carbon-bridged ansa-metallocenes: Knüppel, S.; Erker, G.; Fröhlich, R. Angew. Chem. 1999, 111, 2048-2051;
22. Angew. Chem., Int. Ed. 1999, 38, 1923-1926.
23. Bai, S.-D.; Wei, X.-H.; Guo, J.-P.; Liu, D.-S.; Zhou, Z.-Y. Angew. Chem. 1999, 111, 2051-2054;
24. Angew. Chem., Int. Ed. 1999, 38, 19261928,
25. Synthesis of [3]ferrocenophanes: Knüppel, S.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 1999, 586, 218-222.
26. Knüppel, S.; Fröhlich, R.; Erker. G. J. Organomet. Chem. 2000, 595, 307-312.
27. Liptau, P.; Knüppel, S.; Kehr, G.; Kataeva, O.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2001, 637-639, 621-630.
28. Optical resolution: Liptau, P.; Tebben, L.; Kehr, G.; Wibbeling, B.; Fröhlich, R.; Erker, G. Eur. J. Inorg. Chem. 2003, 3590-3600;
29. 2003, 4261.
30. See for a comparison: Cayuela, E. M.; Xiao, L.; Sturm, T.; Manzano, B. R.; Jalón, F. A.; Weissensteiner, W. Tetrahedron: Asymmetry 2000, 11, 861-869.
31. Manzano, B. R.; Jalón, F. A.; Gómez-de la Torre, F.; López-Agenjo, A. M.; Rodríguez, A. M.; Mereiter, K.; Weissensteiner, W.; Sturm, T. Organometallics 2002, 21, 789-802.
32. Liptau, P.; Seki, T.; Kehr, G.; Abele, A.; Fröhlich, R.; Erker, G.; Grimme, S. Organometallics 2003, 22, 2226-2232.
33. Liptau, P.; Tebben, L.; Kehr, G.; Fröhlich, R.; Erker, G.; Hollmann, F.; Rieger, B. Eur. J. Org. Chem. 2005, 1909-1918.
34. Widhalm, M.; Nettekoven, U.; Mereiter, K. Tetrahedron: Asymmetry 1999, 10, 4369-4391.
35. For ferrocenes see: Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389-5393.
36. Gokel, G.; Marquarding, D.; Ugi, I. J. Org. Chem. 1972, 37, 3052-3058.
37. For ferrocenophanes see: Tainturier, G.; Chhor y Sok, K.; Gautheron, B. C. R. Acad. Sci. Paris, Ser. C. 1973, 1269-1270.
38. Chhor y Sok, K.; Tainturier, G.; Gautheron, B. Tetrahedron Lett. 1974, 25, 2207-2208.
39. Chhor y Sok, K.; Tainturier, G.; Gautheron, B. J. Organomet. Chem. 1977, 132, 173-189.
40. Tebben, L.; Kehr, G.; Fröhlich, R.; Erker, G. Synthesis 2004, 1971-1976.
41. Nilewski, C.; Neumann, M.; Tebben, L.; Fröhlich, R.; Kehr, G.; Erker, G. Synthesis 2006, 2191-2200.
42. Liptau, P.; Neumann, M.; Erker, G.; Kehr, G.; Fröhlich, R.; Grimme, S. Organometallics 2004, 23, 21-25.
43. 3J value became so small that it was no longer observed; see for example: Tebben, L.; Kehr, G.; Fröhlich, R.; Erker, G. Eur. J. Inorg. Chem. 2008, 2654-2658.
44. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis; Springer: New York, 1994.
45. IIDQ mediated peptide synthesis: Kiso, Y.; Yajima, H. J. Chem. Soc., Chem. Commun. 1972, 942-943.
46. Kiso, Y.; Kai, Y.; Yajima, H. Chem. Pharm. Bull. 1973, 21, 2507-2510.
47. For the use of additional DMAP see: Baxendale, I. R.; Ley, S. V.; Smith, C. D.; Tranmer, G. K. Chem. Commun. 2006, 4835-4837.